Penicillin salts of aminophenylpiperidine



Patented Mar. 31, 1953 UNITED STATES PATENT OFFICE PENICILLIN SALTS OF AMINOPHENYL- PIPERIDINE Harley W. Rhodehamel, J r., Indianapolis, Ind., assignor to Eli Lilly and Comp any, Indianapolis, Ind., a corporation of Indiana No Drawing. Application February 13, 1952, Serial No. 271,427

2 Claims. (01. zoo-239.1) 1 2 This invention relates to a novel penicillin salt Example 2 and the preparation thereof. To an a o queous solution 01 .3 g. of the potassium 93W eg g gf g tgg salt of penicillin G in .8 m1. of water is added a p i 1.116 15 Sa 5 can e me W1 solution of .3 g. of N-(o-aminophenyl)-piperidine penicillin or its salts by neutralizatlon or met- 5 in 5 m1 of Water The mixture is cooled and ihq i ifi g g z sparingly sgluble stirred occasionally whereupon the slightly solufm i 5a y a or mails 0 ble N-(o-aminophenyl)-piperidine salt of peniciL- cipitating penicillin from solut1on, and of p-uri- 1m G precipitates The t i separated and tying penicillin. Moreover, the novel penicillin dried invacuo salt can be utilized therapeutically. A prolonged w N (o aminophenyl) piperidme can be prepared pt i blood level can be secured upon by condensing o-mtrochlorobenzene with piperimmlstermg the salt parentemny by method-S dine, and reducing the condensation product known to the medical art.

The following examples illustrate the preparacatalytlcauy Wlth hydrogen and platmum Cate tion of the novel Salt of this invention: 15 i a Example 1 1. The N-(o-aminophenyl)-piperidine salt of penicillin represented by the following formula 1 To 5 g. of a so-uti0n of penicillin (e. g. a com in which P represents penicillin:

mercial mixture of the several penicillins) dissolved in 50 ml. of amyl acetate are added 5 g. CH CH of N-(o-aminophenyl)-piperidine dissolved in 20 P 10 ml. of amyl acetate. The mixture is cooled N and stirred occasionally whereupon the N-(ocHi0i aminophenyD-piperidine salt of penicillin precipitates. The salt is isolated as by decantation The N-(o-ammophenyn-p1peridine salt of or filtration, and dried in vacuo. 25 Pemcimn The salt is represented by the following formula HARLEY RHODEHAMEL.

in which P represents penicillin:

Griz-CE: Q

No references cited. 

1. THE (-O-AMINOPHENYL)-PIPERIDINE SALT OF PENCILLIN REPRESENTED BY THE FOLLOWING FORMULA IN WHICH P REPRESENTS PENCILLIN: 